A new type of anomalous ozonolysis in strained allylic bicycloalkan-1-ols

Tetrahedron Letters

Volumn 46, Issue 31, 2005, Pages 5157-5159

  García Martínez, Antonio ^a   Teso Vilar, Enrique ^b   García Fraile, Amelia ^b   De La Moya Cerero, Santiago ^a   Lora Maroto, Beatriz ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

Bicycles; Cleavage reactions; Ozonolysis; Substituent effects

Indexed keywords

ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; BORNANE DERIVATIVE; CARBOXYLIC ACID; KETONE DERIVATIVE;

ARTICLE; OZONOLYSIS; REACTION ANALYSIS;

EID: 21344455701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.136     Document Type: Article

References (21)

1. Some interesting reviews are P.S. Bailey Ozonization in Organic Chemistry Vol. 2 1982 Academic Press New York
2. R.L. Kucklowski Acc. Chem. Res. 16 1983 42
3. S. Patai The Chemistry of Hydroxyl, Ether and Peroxide Groups 1993 Wiley Chichester Suppl. E2, pp 687-784
4. For example see D.J. Everest, P.K. Grant, G.C. Slim, and I.K.L. Yeo Aust. J. Chem. 41 1988 1025
5. M.P. DeNinno J. Am. Chem. Soc. 117 1995 9927
6. M.E. Jung, and P. Davidov Org. Lett. 3 2001 627
7. For example see J.C. van Velzen, W.C.J. van Tunen, and T.J. De Boer Recl. Trav. Chim. Pays-Bas. 105 1986 225
8. H. Yamakoshi, S.-I. Kawamura, M. Nojima, H. Mayr, and J. Baran J. Org. Chem. 61 1996 5939
9. H. Perg, D.M. Otterness, R.T. Abraham, and L.H. Zalkow Tetrahedron 57 2001 1891
10. M. Francavilla, T. Gasperi, M.A. Loreto, P.A. Tardella, and M. Bassetti Tetrahedron Lett. 43 2002 7913
11. For example see S. de la Moya Cerero, A. García Martínez, E. Teso Vilar, A. García Fraile, and B. Lora Maroto J. Org. Chem. 68 2003 1451
12. A. García Martínez, E. Teso Vilar, A. García Fraile, S. de la Moya Cerero, and B. Lora Maroto Tetrahedron: Asymmetry 14 2003 1607
13. A. García Martínez, E. Teso Vilar, A. García Fraile, S. de la Moya Cerero, and B. Lora Maroto Tetrahedron: Asymmetry 15 2004 753
14. A. García Martínez, E. Teso Vilar, A. García Fraile, S. de la Moya Cerero, and B. Lora Maroto Tetrahedron 61 2005 3055
15. 2S (0.3 mL), allowed to warm up to room temperature and treated with water (10 mL). After standard work up, the obtained residue was analyzed by RMN (3b / 4b in an approximately 4:1 ratio); 74 % yield. Spectroscopic data of 3b are coincident with the previously described by the same compound in Ref. 8, whereas the corresponding data of 4b are coincident with the previously described by us for such compound in Ref. 9.
16. L.A. Paquette, C.A. Teleha, R.T. Taylor, G.D. Maynard, R.D. Rogers, J.C. Galluci, and J.P. Springer J. Am. Chem. Soc. 112 1990 265
17. A. García Martínez, E. Teso Vilar, A. García Fraile, S. de la Moya Cerero, P. Martínez Ruiz, and L.R. Subramanian Tetrahedron: Asymmetry 7 1996 2177
18. Some related pinacolic Wagner-Meerwein rearrangements (e.g., in the treatment of alcohol 1b with m-CPBA) are described in Ref. 6a. Paukstelis has also reported partial formation of analogue 10-hydroxycamphor 3a in the ozonization of 1a under unreported conditions J. Paukstelis, and B.W. Macharia Chem. Commun. 1970 131
19. 2 disengagement of 7b, see: B. Danieli, G. Lesma, G. Palmisano, and B. Gabetta J. Chem. Soc., Chem. Commun. 1981 908
20. At this stage, crude attempts to rule out the claimed stereocontrol empirically (in the base of the restricted disposable experimental data) have resulted to be highly speculative.
21. Diastereoselectivity in the addition of ozone to carbon-carbon double bonds has been reported previously. An interesting work is: M. Miura, M. Nojima, S. Kusabayashi, and K.J. McCullough J. Am. Chem. Soc. 106 1984 2932